Caribbean Regatta Preview: January to March 2020

The ‘peak season’ for Caribbean yacht racing is the first three months of the year, when the weather is the coldest in northern climates and hottest for keen competition in the tropics. Here’s a sampling of what’s coming up and where you can get on the start line with your boat, as crew or on charter during this prime time of the year:

January 17 – 23:
Round Barbados Sailing Week
Thirty-five to 50 boats, including Blue Peter, Spirit of Juno and Conviction, plus schooners Ruth and Tres Hombres are among those registered. New, the main event Mount Bay Round Barbados Race will be run counterclockwise (southabout). “Yachts that have taken part in race before can have a completely new experience in the same place,” says Mike Krimholtz, vice commodore of the Barbados Cruising Club. “The course is particularly favored by smaller boats and multihulls. Whether sailing northabout or southabout is faster remains hotly contested and will have to wait until January 21 to see who is right.”


Kiteboarder Mike Hirst set a new record for the Nanny Cay Challenge. © Broadsword Communications
Kiteboarder Mike Hirst set a new record for the Nanny Cay Challenge. © Broadsword Communications

January 18:
Nanny Cay Round Tortola Race
Sail around Tortola or enter the Nanny Cay Challenge, which expands the circumnavigation course to include Scrub Island, Guana Island and Great Camanoe. All records were broken last year, with a new fastest time set at 1 hour 57 minutes and 15 seconds by the Bieker 53 Catamaran, Fujin. This year, at least six Corsair trimarans are expected to compete. “This event offers a unique opportunity to see the islands from a different perspective and enjoy the post-race party at the famous Nanny Cay Beach Bar,” says Tamsin Rand, manager of the host Royal BVI Yacht Club.


January 18 – 19:
San Sebastian Vela Cup
The Academia de Vela at Puerto Rico’s Club Nautico de San Juan hosts this regatta, which is timed to coincide with the world-famous ‘Fiestas de la Calle San Sebastian’, where over a quarter million people party until midnight in neighboring Old San Juan. This sailing event is one of the island’s qualifiers for the 2020 World Optimist Championship, to be held this summer in Italy. In keelboats, at least two IC24 teams from the US Virgin Islands are expected to compete. 


Grenada Sailing Week - Perseverare Diabolicum. Photo: Tim Wright
Grenada Sailing Week – Perseverare Diabolicum. Photo: Tim Wright

January 26 – 31:
Island Water World Grenada Sailing Week
Forty to 50 boats including Touch2Play Racing, Liquid, TAZ, C-Mos and The Blue Peter, the latter of which celebrates its 90th anniversary on the regatta’s lay day, are registered to race. New, luxury beachfront resort, Silversands Grenada, on Grand Anse Beach, is a race day sponsor thus enabling guests to watch the starts in style. New too is the location of the final night party, says regatta director, Karen Stiell. “Racers and party goers are invited to the ‘Aquarium’ on Magazine beach, a super stunning location – there couldn’t be a better place for the Mount Gay Red Cap Grand Finale party to be!”

February 14 – 16:
Jolly Harbour’s Valentine Regatta
New, the first race is be spectator-friendly with a start right in the Jolly Harbour Marina. Some 20 sailboats are expected to race. “The courses last year were based on the Olympic model (cannon and reach),” says Grahame Williams, commodore of the host Jolly Harbour Yacht Club. “That was very successful. So, we will be doing it again.”


February 14 – 16:
Caribbean Multihull Challenge
This second annual event is open to all multihull sailors on racing catamarans and trimarans as well as chartered cats and cruising multis, according to Stephen Burzon, St. Maarten Yacht Club board member. New, sponsor Oris is offering a prized timepiece for the multihull that races in both this event and the St. Maarten Heineken Regatta and achieves the best combination score.

February 15 – 16:
Sweethearts of the Caribbean and Classic Yacht Regatta
The BVI’s West End Yacht Club hosts this ages-old event out of Soper’s Hole, Tortola, with this being the second year both the captain’s meeting and awards held at the new clubhouse, located at Omar’s Fusion restaurant. “We expect around 20+ entries, with sailors coming from the USVI and Puerto Rico.  We plan to have monohulls, catamarans and trimaran included in this year’s race, and hope to bring back the couples race as well,” says organizer, Kelly Bennett.


March 5 – 8:
St. Maarten International Regatta
Known for its Serious Fun tag line, the regatta celebrates its 40th anniversary with a view to the next five years with a new race director at the helm. The anniversary theme runs throughout the event, on the water and off, with surprises planned, says general manager, Michelle Korteweg. “The Volvo’s will be represented significantly in 2020, with Team Childhood, formerly Team Brunel, and Maiden Factor. Other entries are a MOD70 Argo, participants from Dominican Republic and a good turnout from Russia and Poland again. In addition, approximately 50 bareboats will join the already existing entry list, so already we are close to 100 entries.” 

March 6 – 8:
St. Croix International Regatta
New courses are the highlight of this regatta, with its signature skipper’s weight in rum prizes in all main event classes with 6 or more paid entries. “The courses are more suitable for cruisers, live-aboard cruisers and multihulls, for example around Buck Island (whale sightings are common this time of year), Salt River, Grassy Point, also Christiansted Harbour,” says Juliet San Martin, who co-directs the St. Croix Yacht Club-hosted event with Karen Stanton. There’s also an Optimist dinghy event for advanced and green fleets held at the same time.

March 11 – 15:
Superyacht Challenge Antigua
Record attendance is expected for this 10th anniversary event, designed solely for the pleasure of superyacht owners, their guests and crew. Five J Class yachts – Lionheart, Ranger, Svea, Topaz and Velsheda – are expected to make their debut. Other entries include favorites such as Sojana, Pink Gin and Adela.


Gustavia Harbor. Photo: Ed Gudenas

March 19 – 22:
St. Barths Bucket Regatta
Over 30 superyachts are expected to compete, including four J Class yachts – Lionheart, Topaz, Svea and Velsheda, with a special day of windward/leeward racing on March 19. Also back are the 115’ and 148’ Baltic yachts, Nilaya and Visione; the 157’ Royal Huisman, Wisp; and 180’ Pendennis, Adela. “The Bucket is famous for its traditional and enduring characteristics,” says event manager, Jeanne Kleene. This year’s Bucket Bash and Prizegiving Ceremony will be held on the beautiful grounds of the Collectivité.


March 27 – 29:
St. Thomas International Regatta
One-design sailing is a signature of this event, with over 20 IC24s expected on the start line. CSA Racing, Cruising and Bareboats; Large Multihulls; Beach Cats and other One-Design over 20’ are welcome. The host St. Thomas Yacht Club boasts a new beachfront dock, following hurricane damage to the old one in 2017. “We are known as the ‘friendly regatta’ as we cater to all your needs before and doing the event,” says regatta director, Bill Canfield.


March 30 – April 5:
BVI Spring Regatta and Sailing Festival
New cutting edge classes have long been a feature of this nearly half-century strong event, hosted at the Nanny Cay Resort & Marina. Performance Cruising is a 2020 addition. “This class allows the race boats with full interiors to sail with their racing inventories, including spinnakers, against like boats,” says race committee chairman, Robert Phillips. The Sport Multihull class, which was added last year, welcome six Corsair trimarans. Overall, there’s over 15 classes, five days of racing, three bodies on which to compete and plenty of parties every night, invites director, Judy Petz.

Carol M. Bareuther, RD, is a St. Thomas, U.S. Virgin Islands based marine writer and registered dietitian.